Carbonyl oxides will be investigated as oxenoid reagents and as possible mimics of the monooxygenase enzymes (MOX). The carbonyl oxides will be produced via singlet oxygen oxidation of diazo compounds and via ozonolysis of suitable olefins. The substrates to be studied will be chosen from among olefins, aromatic compounds, and amino acids. The objective is to demonstrate that carbonyl oxides can fulfill all of the requirements for a successful MOX model, namely, olefin epoxidation, oxidation of aromatic (including polycyclic) hydrocarbons, and oxidation involving the NIH shift. Substrates will also be chosen so as to determine the relationship between oxidations by carbonyl oxides and the conversion of pre-carcinogens to ultimate carcinogens. Using suitably substituted olefins, the electronic and steric requirements of carbonyl oxides as epoxidation reagents will be studied. Likewise, variously substituted aromatic carbonyl oxides will be studied in order to determine the nature of the carbonyl oxide oxidations.